Workday Buys Sana: A Second Chance for Enterprise Learning?

It’s easy to forget that time is a relative concept. But once in a while, history reminds us we can’t escape the truth. Case in point: Last week’s news that HCM giant, Workday, intends to acquire AI-native learning platform, Sana.

Workday says Sana will make it possible to offer “a new experience, where knowledge, data, actions, and learning converge and create the new front door for work.” Powerful stuff. Yet, Workday spoke in similar terms way back in September 2015, when it revealed plans to build a new homegrown LMS.

A Reality Check From the Past

That original Workday Learning announcement was 10 years ago, but it seems like only yesterday to me. At that time, I wrote about it optimistically:

Workday wants to change the game by building its own LMS, targeting an increasingly younger, more digitally savvy workforce. The vision is a fully integrated LMS, capable of managing any type of learning — from formal to informal — with a modern mobile, social, continuous, contextual experience.

The bar is low in the HR/Talent LMS space. This means Workday can knock it out of the park, just by following the blueprint of standalone LMS specialists, with an engaging platform that looks and acts more like Facebook and less like a database.

If Workday succeeds, this will be one of the only HR/Talent learning systems that can also compete in standalone platform opportunities. This will cause heartburn among current tier 1 standalone LMSs, as well as HR/Talent LMS providers.

Why was I so hopeful a decade ago? By deciding to build rather than buy, Workday was being true to its enterprise cloud DNA. The idea was simple: Create a learning platform that would fully integrate with its HCM suite and sell it into its enormous installed base.

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What Was Missing?

Despite the huge potential upside, I saw a glaring gap in Workday’s roadmap. The company offered no support for corporations seeking a more modern, effective way to educate customers, partners, or resellers. The focus was squarely on employee learning.

Still, the extended enterprise opportunity was there, and the industry was watching. Here’s how I put it at the time:

Employee LMSs are about cost savings, compliance, efficiency, and automation. In contrast, learning systems that enable customers, channel partners, and other allies to succeed are about making money.

Of course, Workday’s strength is in HR and Finance. It has precious little experience in non-employee learning. But why overlook a huge opportunity to turn an employee-facing LMS into a solution that serves the needs of external audiences? By leveraging its massive client base, Workday could triple down on the size and value of its LMS sales.

Fast-Forward 10 Years

So, where is Workday Learning today? By and large, this LMS still hasn’t lived up to its promise. Capabilities lagged. Clients haven’t been impressed. Market momentum has never materialized. And the extended enterprise gap? Never closed.

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Why Is Sana Important?

Last week, Workday changed course by announcing its plans to pay $1.1 billion for Sana Labs. What does this move really mean?

In a world where AI buzz is deafening, this Swedish startup has been receiving attention for all the right reasons. For instance, Sana is the genius behind breakthrough learning applications such as Galileo Agent and Galileo Learn, from The Josh Bersin Company. (For more information about how these AI-powered HR solutions work, check my recent interview with Josh on the Talented Learning Show podcast.)

Clearly, this Workday investment is much more than an LMS product update. It’s a strategic pivot. After a decade of organic effort that underwhelmed, Workday is now betting big on acquisition to reinvent its corporate learning story.

Why Does Sana Matter Now?

Founded in 2016, Sana has built a reputation as a highly innovative AI-first learning platform. The brand rapidly became known for its intuitive design, conversational interfaces, and ability to personalize learning at scale, among other things.

Because Sana has been way ahead of the pack in bringing generative AI, agentic workflows, and knowledge automation to market, it has gained a strong competitive advantage. That’s especially true when you compare Sana with traditional LMS platforms — many of which are frantically playing catch-up. That is precisely the kind of technology leadership Workday Learning needs.

Although vendors like Absorb, CYPHER, Cornerstone, Docebo, and Schoox are racing to release AI copilots and assistants, Sana brings instant credibility and product depth to Workday in this fast-moving space.

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With Sana, Will Workday Make the Same Mistake Twice?

If you think the biggest growth segment in learning today is employee skilling, think bigger. Think about  go-to-market education — where business success depends on educated customers, partners, resellers, and frontline sales and support.

These external-facing programs drive revenue, retention, and competitive differentiation. They demonstrate measurable business impact. That’s why the learning industry has been shifting its energy in this direction. And it’s where LMS vendors are winning deals every day.

Workday’s track record focuses solely on employee training and development. If this pattern continues, the company will never conquer the broader learning market. So, with or without Sana, it leaves the door wide open for a mosaic of LMS vendors like Eurekos, LearnUpon, Litmos, NetExam, and Skilljar, who will continue to thrive by claiming their fair share of the lucrative extended enterprise space.

The Road Ahead: My Fresh Take for 2025

A decade ago, Workday had the right idea but the wrong scope. Now, 10 years later with Sana, Workday has another chance — this time powered by AI. The Sana acquisition gives Workday a strategic reset in learning, at a huge premium. But the fundamental question remains:

Will Workday finally learn to look outward, beyond employees?

If so, look out.

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